Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides

Yi Feng Wang; Geoffroy Hervé Lonca; Maïwenn Le Runigo; Shunsuke Chiba

doi:10.1021/ol501997n

Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides

Yi Feng Wang, Geoffroy Hervé Lonca, Maïwenn Le Runigo, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

87 Citations (Scopus)

Abstract

Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me₃SiR_f (R_f = CF ₃, C₂F₅, and C₃F₇) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI(OAc)₂. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which subsequently cyclize with the intramolecular arene moiety, furnishing aza-PAH skeletons having polyfluoroalkyl (R_fCH₂) function.

Original language	English
Pages (from-to)	4272-4275
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	16
DOIs	https://doi.org/10.1021/ol501997n
Publication status	Published - Aug 15 2014
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides",

abstract = "Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF 3, C2F5, and C3F7) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI(OAc)2. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which subsequently cyclize with the intramolecular arene moiety, furnishing aza-PAH skeletons having polyfluoroalkyl (RfCH2) function.",

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T1 - Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides

AU - Wang, Yi Feng

AU - Lonca, Geoffroy Hervé

AU - Le Runigo, Maïwenn

AU - Chiba, Shunsuke

PY - 2014/8/15

Y1 - 2014/8/15

N2 - Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF 3, C2F5, and C3F7) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI(OAc)2. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which subsequently cyclize with the intramolecular arene moiety, furnishing aza-PAH skeletons having polyfluoroalkyl (RfCH2) function.

AB - Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF 3, C2F5, and C3F7) are employed as the sources of perfluoroalkyl radicals upon oxidation with PhI(OAc)2. The addition of perfluoroalkyl radicals to biarylvinyl azides generates the corresponding iminyl radicals, which subsequently cyclize with the intramolecular arene moiety, furnishing aza-PAH skeletons having polyfluoroalkyl (RfCH2) function.

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Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides

Abstract

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